Process for preparing 4-aminodiphenylamine
a technology of aminodiphenylamine and aminodiphenylamine, which is applied in the preparation of organic compounds, amino compounds, organic chemistry, etc., can solve the problems of reducing the yield of valuable 4-adpa, reducing the volume productivity of this reaction, and reducing the total reaction time.
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example a
nal Coupling Reaction of Aniline with Nitrobenzene
[0107]This example illustrates the results obtained when laboratory experiments were conducted similar to Example 13 of U.S. Pat. No. 5,608,111.
[0108]The coupling reaction was carried out in a 2 liter Glass Round Bottom flask (RB flask) equipped with a stirrer (½ moon blade Teflon™ stirrer), Dean-Stark condenser, thermometer, Teflon™ baffle, dropping funnel for nitrobenzene addition. Initially 25% aqueous TMAH solution (24.8% w / w, 680.7 gm, 168.8 gm on 100% basis, 1.86 moles) was charged into the RB flask. Water was removed by distillation under reduced pressure at 55 mm Hg to obtain an aqueous TMAH solution of 35% w / w TMAH. During this stage the temperature increased to 50-53° C. Aniline was charged (1003.9 gm, 10.76 moles) into the reactor and the distillation was continued under reduced pressure at 55 mm Hg. Water and aniline were removed by azeotropic distillation until the molar ratio of water to TMAH was about 4:1. During this ...
example 1
of Nitrobenzene in a Single Lot
[0112]This example illustrates the effect of addition of nitrobenzene in single lot after attaining the desired water to base mole ratio for the start of the coupling reaction, and its impact on volume productivity.
[0113]The reaction set up was the same as was used for Example A. Initially, aqueous TMAH solution (35% w / w, 480.5 gm, 168.18 gm on a 100% basis, 1.85 moles) was charged. Aniline was charged (1004.2 gm, 10.8 moles) into the reactor and distillation under reduced pressure was continued at 55 mm Hg. Water and aniline were removed by distillation until the molar ratio of water to TMAH was about 4:1. During this process the temperature of the reaction mass increased to 75° C. After attaining required mole ratio of water to base, nitrobenzene (218.7 gm, 1.78 moles) was added in single lot by using a dropping funnel. After nitrobenzene addition, water and aniline were continuously removed from the reaction by distillation under reduced pressure at...
example b
of the Coupling Reaction Product
[0116]This example illustrates a typical example of reduction of 4-NODPA and 4-NDPA in coupling mass.[0117]In 2 liter capacity autoclave, a coupling reaction product (900 gm) containing aniline (54%), TMA salt of 4-NODPA (25%), 4-NDPA (1.8%), phenazine (0.3%), azobenzene (1.8%) was placed. To this product was added water (307 gm) and noble metal catalyst (e.g. 5% Pd / C, 4 weight % loading on 4-NODPA+4-NDPA). The reaction mixture was heated at 80° C. under a hydrogen pressure of 15 kg / cm2. At the end of reduction (no hydrogen absorption, typically 30 minutes), the unconverted 4-NODPA and 4-NDPA content was almost negligible (
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